The best sailing holidays to keep the entire tribe happy (2023)

Let’s face it, July and August are not the ideal months to visit the Med. Overcrowded and overheated, it’s not the time to go if you’re looking for peace and pleasure. Come September, though, the heat is losing its sting, the schools are back and, for a spot of true tranquility, now is the moment to take to the water. Sailing, after all, is not just for sailors these days.

There is no need – unless you want to – to be hauling ropes and swabbing decks. You can have an entire crew sailing you from tiny port to secluded bay and waiting on you hand and foot in the meantime. If you do want to learn to sail yourself, though, there are plenty of opportunities to try under the expert guidance of an experienced skipper.

There are vessels for every taste, too. If you’re historically inclined, there are replicas of the sort of three or four masted schooners Captain Onedin would have sailed (with rather more creature comforts, of course). There are catamarans and motor yachts or, for a more exotic touch, Turkish gulets. If expense is no object, you can charter an entire boat and host your family and friends. Or if you want to – as it were – just dip a toe in the water, you can book a cabin for a few nights to see whether sailing is for you. You’ll almost certainly be back for more.

The total relaxation option

If what you want is total R&R – with a crew doing all the hard work and a chef offering tasty delicacies all day long – there are plenty of choices available. So if your ideal way of hitting the high seas involves beautiful seascapes and the wind in your hair (from the comfort of your lounger) – look no further.

Enjoy the Aegean on a sleek catamaran

If you want to make something of an entrance when you arrive in port, Meridian Adventure Sail have fully crewed 62ft sleek, high-tech catamarans. They have privacy and comfort by the bucketload, three or four double en-suite cabins and a dedicated crew. You can charter a single catamaran or larger groups can even take a pair.

This is your own private boat for a week so you choose your own itinerary, too, from the Iconic Aegean (Cesme, Chios, Mykonos, Antiparos, Paros, Naxos, Kalimnos, Bodrum) or the Undiscovered Aegean (Kusadasi, Samos, Patmos, Kalminos, Kos, Knidos, Datca, Bozburun, Dalaman, Limani, Gocek). There will be deep blue waters whichever you go for, plus a mix of Turkish and Greek cultures and food, as well as lots of activities available both sea and land based.

How to do it: Meridian Adventure Sail (00 27 079 178 7867; offers a whole boat charter price from £47,165, from September 11-18 with all meals and drinks included. There are further sailings until 15 October.

Sail the islands and coasts of Italy

If you hanker for the romance of the 19th century, though, you might be tempted by Star Clippers. With three of the world’s largest and tallest fully crewed sailing ships, they replicate historic ships but have state-of-the-art navigation systems and modern comforts (no hammocks here, I promise). Star Clipper is 115 metres long with four masts, spacious decks (there are two pools) and carries 166 guests. She can travel at up to 17 knots (when you’ll certainly feel the wind in your hair).

How to do it: Star Clippers (0845 200 6145; has a 10-night trip from £2,199 per person (excluding flights) and including a three-night pre-cruise stay in Rome at The Guardian. After this you leave and return to Civitavecchia (the port for Rome) on board Star Clipper, visiting the Aeolian Islands, Sicily, the Amalfi coast, Sorrento and the Pontine islands. Departing September 21, 2022.

Watch islands drift by on a yacht around Corfu

Fleewinter currently have their 65ft super-yacht Argentous based in Corfu (and have knocked 15 per cent off the price for week-long charters in September). The yacht comes with a skipper and a chef and it sleeps eight people, visiting a new island every day. On board there are plenty of activities (paddleboards and water skiing, for instance) but you do as much or as little as you please. You can even help the skipper if you feel like it though sipping a G&T while watching the islands drift by is certainly a delightful option.

How to do it: A week in September costs £1,830 per person (excluding flights and transfers) for a full charter of Argentous and includes breakfast and lunch. Dinner and alcohol are not included in the price, but paid separately at the end of the trip (020 7112 0019;

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Feel like a star around the Greek islands

For a bit of old-style Hollywood glamour, you could visit the Greek islands on the vintage motor yacht Maid Marian 2. She was extensively overhauled last year on her 90th birthday, retaining her vintage charm but adding everything you could possibly think of by way of mod cons.

She is one of a handful of pre-war classics in the Med and she’s owned by Hollywood film director Roland Emmerich (The Patriot, Godzilla, Independence Day). Available only as a full charter, Maid Marian 2 sleeps up to 10 adults. She is your boat (for a week) so you decide on the itinerary – the captain will help you decide but you could start, say, in Athens (friends can board en route if they like – pick-ups at other ports are no problem) and go on to visit such islands as Kythnos, Serifos, Sifnos, Paros, Antiparos, Mykonos and more.

How to do it: A seven-night luxury trip between May and September (there is still some availability for September 2022 as well as next year) costs around £60,000 (

Discover deserted beaches in Sardinia

The beautiful Italian island of Sardinia is a great place for a spot of circumnavigation. The luxury Dream Yacht Charter catamaran will sail you around the whole island and with just six en-suite cabins, she has a floating house party atmosphere on board. You can book your own cabin with Dream Yacht Charter (rather than chartering the whole boat – though this is another possibility) and make your own plans daily, meeting up with the other guests at the end of the day to enjoy meals and drinks (all included in the price).

There are kayaks and snorkelling equipment on board for exploring Sardinia’s beautiful white sandy beaches and on this trip the aim is to discover the most deserted ones, though you do also get to visit small towns and harbours for shopping and sightseeing.

How to do it: Dream Yacht Charter (02380 455 527; has a seven-night by-the-cabin cruise around Sardinia on June 17, 2023 for £1,849 per person, flights not included.

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Be as hands on or off as you like

If you would really like to try your hand at actually sailing the boat, there are plenty of alternatives available. You don’t need any previous experience, as these trips quickly make up for lost time, meaning you’ll learn a lot about navigation and get involved in the day-to-day running of the vessel – though with plenty of time off for swimming and relaxing, too.

Test your skills around Portugal, Spain and Gibraltar

For a truly historic sailing experience, try VentureSail’s traditional tall ship Blue Clipper, an impressive three-masted gaff rig schooner. You’ll sail from Portimao in Portugal to explore the Algarve region, Cadiz in Spain and then head south to Gibraltar. So while you’re not strictly speaking in the Med, you’ll certainly glimpse it from Gibraltar while actually spending most of your time on the Atlantic. And you are, in the best sense, very much at sea here.

Even if you have no sailing experience, you will find yourself hoisting sails, tying knots, heaving ropes and even taking the helm – the crew are always on hand to guide you. There are just six en-suite twin cabins with twin bunks and there’s one family cabin that sleeps six. All your meals are included, along with soft drinks and a glass of wine at dinner. Expect hearty, home-cooked meals from the chef – after all, you’ll be hungry after a long day in the salty air. There are three kayaks and three paddle-boards for guest use while at anchor.

How to do it: VentureSail Holidays (01872 487288; has an eight-day sailing between October 28-November 4, priced from £1,645 per person (excluding flights)

See dolphins and whales in the Ligurian Sea

Interested in conservation? Head to the Ligurian Sea off the Italian coast with Responsible Travel and get involved not just in sailing the boat but researching vulnerable dolphin and whale populations. No experience of sailing or conservation research is needed – just a willingness to get stuck in. Full training is given in computer data entry, hydrophone listening, checking course and speed, and whale and dolphin monitoring. Being a full crew member also involves a certain amount of housekeeping – for instance, shopping in the local markets. There is plenty of time to swim and sunbathe in between.

How to do it: Responsible Travel (01273 823700; has departures every Monday from San Remo throughout September (with groups of six-11 people on board) from £676 per person (excluding flights) for five nights in a shared cabin on a 21-metre motor sailer.

Relax along Italy’s glorious Amalfi coast

If you want a taster to decide whether sailing is really for you, opt for Intrepid Travel’s short sailing holiday along Italy’s glorious Amalfi coast. Over just four days you visit Amalfi, Capri and Procida on board a Bavaria 51 sailboat – the perfect yacht for novices to learn the ropes and help the crew on deck.

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It’s not compulsory, though, so you can just relax and enjoy the view, if you prefer. You have plenty of time in port, too, where you can explore olive groves, pastel cliffside villages, ancient cities and pebbled beaches with a local guide to show you the way. There’s a visit to Capri’s Grotta Azzurra (Blue Grotto) and you can swim from the yacht in the clear waters of the Med.

How to do it: Intrepid Travel (0808 274 5111; has four days from £635 per person (excluding flights) including on-board accommodation, transport, selected meals and activities.

Explore Croatia's secret beaches and swim in hidden coves

Croatia is renowned for its stunning coastline, but its beauty can be somewhat marred by the crowds. Enter G Adventures, who aim to take you away from the busy bits on an eight-day sailing trip down the Dalmatian coast on a 52ft yacht. The group will be just eight travellers and you can explore secret beaches, swim in hidden coves, kayak through gorgeous inlets and hike across the island of Mljet – a place so beautiful that Odysseus stayed there for seven years. Get your fix of local culture and nightlife on shore before retiring to the peace of your cabin – the skipper can give you lots of recommendations, and – if you want to – also give you the opportunity to learn the ropes even if you have no sailing experience.

How to do it: G Adventures (0207 313 6937; has this eight-day trip from £1,015 per person when booked by 31 August (excluding flights, food and drinks) for September departures from Split to Dubrovnik.

Blend sea and land

Combine a chartered boat holiday with some guided hiking

Of course, lying around on deck all day with your own chef on hand can have a deleterious effect on the waistline. So Not in the Guidebooks suggest combining your own fully crewed chartered boat with some hiking through the Greek Dodecanese Islands. Starting in Kos and finishing in Rhodes, you visit the lesser known islands of volcanic Nisyros, empty Tilos, even more deserted Alimia, vibrant Symi and laid-back Halki with the meltemia (Northern winds) in your sails.

There are three island hikes (including around the volcanic crater of Nisyros) and a couple of town walks with your guide. You have four nights on board and a night in a boutique hotel on Rhodes (at the start) and Kos (at the end), as well as a cookery class on Symi.

How to do it: Not in the Guidebooks ( has this six-night sailing from £3,742 per person in September and £2,799 per person in October, including all meals on board and five local taverna dinners, but not flights.

Something a bit different

Explore the eastern corner of the Med on a Turkish gulet

The traditional Turkish wooden gulet has become a traveller favourite over recent years, and chartering a whole boat or joining a group to explore the eastern corner of the Mediterranean makes a wonderfully novel sailing experience.

Salamander has two beautiful gulets that have recently been extensively refurbished. Ya Salam (the slightly bigger of the two, at 87ft and sleeping up to 14 guests in seven en-suite cabins) is available September 24 to October 1 on a round trip – departing and returning to from Bodrum in Turkey. You charter the whole boat – making it a great alternative to a Turkish villa holiday – and the coast of Turkey makes for a fascinating sail, dotted with ancient cities, hidden coves, secluded beaches and quaint seaside villages.

When you’re not visiting the sites on land, you can play with the on-board water toys (donut, ringo, paddle boards, snorkelling, canoes), while daily breakfasts, lunches and afternoon teas are included, as well as five dinners (leaving you a couple of nights for dinner on dry land, should you wish) and all house drinks.

How to do it: Salamander Voyages (07887 874886; has this seven-night private charter for £16,250 (£1,355 per person) based on 12 guests sharing and excluding flights.

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Make friends with like-minded travellers on a gulet

If you want to try the gulet experience with some like-minded strangers instead of chartering your own boat, Friendship Travel has a round trip from Fethiye where all you have to do is book your own cabin. Sailing across the Aegean you visit Oludeniz, the islands of Gemiler and Tersane as well as Bedri Rahmi Bay, Kleopatra Port, Tarzan Bay and the Yassica Islands.

The traditional wooden gulets have eight cabins – and you’ll have a double or twin for your sole use as a single traveller. They are fully crewed, though guests are welcome to learn how to sail, too, if they wish. You stay in a different anchorage every night and there is plenty of opportunity for swimming, snorkelling and sea kayaking.

How to do it: Friendship Travel (0289 446 2211; has seven nights for £1,470 per person (with flights from London Gatwick or one of several regional UK airports) departing Fethiye September 5, 12 and 19 and including full board and use of water sports equipment.

For full details of entry requirements and Covid rules for your favourite destinations, see Refer to for further travel information.

Would you try a sailing holiday? Please let us know in the comments below


Where is the best sailing in Europe? ›

The best places for sailing in Europe
  • The Ionian Coast, Greece.
  • The Dalmatian Coast, Croatia.
  • The Balearic Islands, Spain.
  • Cote d'Azur, France.
  • The Amalfi Coast, Italy.
  • Corsica, France.
  • The Turquoise Coast, Turkey.

What are flotilla holidays? ›

WHAT IS A FLOTILLA SAILING HOLIDAY? A flotilla is a group of 10-12 yachts, guided by one of our lead boats, with a Skipper, Engineer and Hostess on board. On a flotilla holiday you can meander around the beautiful Greek Islands in the comfort of your own yacht, living the dream.

What is flotilla sailing? ›

Sailing in company on your own yacht ...

A "flotilla" is a group of yachts sailing in company accompanied by a flotilla skipper and hostess on the lead yacht. You have virtually all the advantages of independent yacht charter, plus the support of the flotilla crew to make the most of your flotilla sailing holiday.

Where can I sail in the summer? ›

The 5 Best Places to Sail This Summer
  • Belize. Does an off-the-beaten-path summer escape featuring uncrowded anchorages and charming little beach bars strike your fancy? ...
  • British Virgin Islands. ...
  • Croatia. ...
  • St. ...
  • Thailand.
9 Apr 2018

Where is the safest place to sail? ›

Sail from the Atlantic westward to the Caribbean, using the trade winds, crossing the Panama Canal, the South Pacific Ocean, and then either around Cape of Good Hope or through the Suez Canal. The safest sailing conditions are along the equator since it provides the most reliable sailing weather and calmest waters.

When should I sail to Europe? ›

Peak season is December to April - the perfect time for a warm getaway if you're looking to escape the cold weather in the U.S. or Europe. For fewer tourists and lower prices, sailing during the shoulder season (in May or June) is a good option, too.

How many boats are in a flotilla? ›

Flotillas are typically made up of the same type of ship, and depending on the type of ship, whether it's a submarine or a battleship, determines how many ships are in a flotilla. A flotilla is no less than three ships, but can have as many as twenty.

What is a flotilla skipper? ›

In flotilla sailing you sail as part of a group of boats. Flotilla comes from the Spanish flota – which just means a fleet of ships. You'll have your boat to yourself – just you, your friends and family on board – and a hired skipper as well, if you want some support. You can sail at your own pace.

Is a flotilla? ›

A flotilla is a group of small ships, usually military ships.

What is bareboat charter party? ›

2. Bareboat Charter Party. By this type of charter, the shipowner leases his entire vessel and the charterer has the responsibility of operating it as though it were his own vessel. As the name implies, the bare vessel is chartered.

How big is a flotilla? ›

You can go on a flotilla vacation as a couple and charter a small 32 foot monohull, or take your whole family – and your neighbour's too, and charter a roomy catamaran with room for up to 11 people. Flotilla trips usually last for one week and start on Saturdays.

Where is the sailing capital of the world? ›

Newport Sailing Events and Regattas

Newport, Rhode Island, “sailing capital of the world,” has many other annual sailing events.

Where is the best sailing in the world? ›

The 10 Best Sailing Destinations in the World
  • 01 of 10. South Georgia Island, Southern Ocean. ...
  • 02 of 10. The Galapagos Islands, Ecuador. ...
  • 03 of 10. The Whitsunday Islands, Australia. ...
  • 04 of 10. Zanzibar Island, Tanzania. ...
  • 05 of 10. The Greek Isles. ...
  • 06 of 10. The Adriatic Coast, Croatia. ...
  • 07 of 10. The Bay of Islands, New Zealand. ...
  • 08 of 10.
7 Nov 2020

Where should you avoid when sailing around the world? ›

The Most Dangerous Places to Sail in the World – 7 Areas You Should Avoid!
  • 1 1.Gulf of Guinea.
  • 2 2. Cape Horn.
  • 3 3.The Gulf of Aden.
  • 4 4. Point Conception.
  • 5 5. Straits of Malacca.
  • 6 6. Margarita Island.
  • 7 7. Bermuda.
  • 8 Conclusion.

Is it easier to sail east or west? ›

At tropical latitudes, sailing West-about is usually the easier way. This is thanks to prevailing winds blowing from East to West.” He adds that “sailing at high latitudes is almost exclusively the preserve of Ocean Races.

What boat is best for liveaboard? ›

Which boat types make the best liveaboard vessels? Houseboats, Trawlers and Catamarans make the best liveaboards, although they each vary greatly in their design. Motor Yachts and Express Cruisers are also good options.

How big of a yacht do I need to sail across the Atlantic? ›

In essence, your sailboat shouldn't be less than six feet at it may be too dangerous out there. With that in mind, the best sailboat to cross the Atlantic should measure at least 30 or 40 feet long to be able to withstand the stormy weather and the rough waves and winds.

What month is the Atlantic Ocean the calmest? ›

The calmer time of year lasts for 4.0 months, from May 28 to September 27. The calmest month of the year in Atlantic is August, with an average hourly wind speed of 8.7 miles per hour.

What size boat do you need to go offshore? ›

Best Boat for Offshore Fishing

The best length for a general-purpose offshore fishing boat will fall between 30 to 40 feet, which will handle long-distance travel and most weather conditions.

What is a group of 5 ships called? ›

A fleet is usually a large group of ships, but it can be any group of vessels like planes or cars that operate as a unit. A naval fleet is the largest formation of warships.

What is a group of sailboats called? ›

Flotilla. A group of yachts cruising together. Flying bridge (or Flybridge).

Which is bigger fleet or flotilla? ›

A flotilla (from Spanish, meaning a small flota (fleet) of ships), or naval flotilla, is a formation of small warships that may be part of a larger fleet.

How much do yacht skippers earn? ›

Charter Skipper Salary
80-99 ft.100-119 ft.
Captain$5,000 – $10,000$7,000 – $11,000
Chief/First Mate$3,000 – $4,500$4,000 – $5,500
Bosun$2,500 – $3,000$3,500 – $4,500
Deckhand$2,500 – $3,500$2,500 – $4,000

How much does a flotilla skipper earn? ›

Mediterranean flotilla work is less well paid but the lifestyle is great. A flotilla skipper earns €180 to €300 a week. A couple working together on a busy charter boat in the Caribbean will have joint earnings in the range $50,000 to $90,000 a year.

How long does it take to become a skipper? ›

With your internationally recognised license in hand, you now have the opportunity to take your friends and family sailing on Yachts around the world. I am not surprised if this might feel incredibly daunting as this license can be achieved in as little as three weeks.

What is a small group of boats called? ›

FLOTILLA. a fleet of small craft.

Whats smaller than a fleet? ›

A squadron, or naval squadron, is a significant group of warships which is nonetheless considered too small to be designated a fleet. A squadron is typically a part of a fleet.

What does Flotila mean? ›

1 : a fleet of ships or boats especially : a navy organizational unit consisting of two or more squadrons of small warships. 2 : an indefinite large number a flotilla of changes.

Can you sail around the Azores? ›

Azores Sailing – Overview. The notion of sailing around the Azores is one of romanticism and peace as you gently cruise between the rocky volcanic islands that rise out of the water. Known for being one of the two best sailing spots in Portugal, it has been attracting sailors from all over the world.

How long does it take to sail from Portugal to the Azores? ›

The straight line distance was roughly 800 nautical miles and most people motor straight to there in about 6 to 7 days.

How long does it take to sail to Azores from UK? ›

We will spend just under 9 days at sea, sailing upwind over 1200 nautical miles across the Atlantic to the Azores.

When can you sail to the Azores? ›

Sailing conditions in the Azores:

temperatures average about 13oC in the winter season. the best time for sailing is late April through October. during spring and summer, the conditions are more calm and clear from fog.

What is a good size sailboat to live on? ›

For a sailboat to be considered as a liveaboard, it needs to be at least 30ft. Anything smaller and the boat will be cramped for anyone other than a solo sailor. However, the larger the boat, the greater the cost of ownership. The ideal size sailboat to live on would be 35-45 feet for most people.

Is it cheaper to live on a boat than a house? ›

The cost of living on a boat is considerably less than in a traditional home. You can pick up a half-decent boat for a few thousand pounds and then live rent free if you don't have a permanent mooring, which can be expensive as they're in short supply. There's also no council tax.


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